Ammonia → (1R,3R,4S)-4-bromo-3-hydroxycyclohexanecarboxylic amide

HRID 1437334Notes

Reaction equation

HRID 1437334 reaction equation
[Br:1][C@@H:2]1[C@H:8]2[CH2:9][C@H:5]([C:6](=[O:10])[O:7]2)[CH2:4][CH2:3]1.[NH3:11]>C1COCC1>[Br:1][C@H:2]1[CH2:3][CH2:4][C@@H:5]([C:6]([NH2:11])=[O:10])[CH2:9][C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13076925(1R,4S,5R)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

Product 1

HCID 58743889(1R,3R,4S)-4-bromo-3-hydroxycyclohexanecarboxylic amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,4S,5R)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one (a) (2.13 g, 10.4 mmol) was taken up in THF (20 mL) and treated with 0.88 ammonia (5.3 mL) at 20° C. for 24 hours with stirring. The solvent was then removed in vacuo to give a white solid (2.31 g).

Workup

  1. customThe solvent was then removed in vacuo

Sources & evidence

ORD record
ord-8023f6645c6a432f8076df7c002c56e9
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

Loading…